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  • 11
    Electronic Resource
    Electronic Resource
    Implications of chirality and geometric isomerism in some psychoactive drugs and their metabolites (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 99-120 
    Details
    ISSN: 0899-0042
    Keywords: asymmetry ; enantiomers ; geometric isomers ; (+)- (-)-isomers ; D- and L-isomers ; R- and S-isomers ; Z- and E-isomers ; drug metabolism ; stereoselectivity and stereospecificity in drug action ; stereoselectivity and stereospecificity in drug metabolism ; psychotropic drugs ; stimulants ; antidepressants ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Many drugs contain a chiral centre, or such a centre is introduced during metabolism of the drug in man and in animals. If a single chiral centre is present, the drug will normally exist as a mixture of two enantiomers, of which one may have quite different pharmacologic and/or toxic effects than the other. Chiral drugs that are used in psychiatry, and some other pharmacologically related drugs are identified, and the implications of the presence of one or two chiral centres in these drugs are discussed. Differences in pharmacologic properties of drug and metabolite enantiomers are identified and discussed. Also reviewed are the properties of some drugs used in psychiatry that both are chiral and display geometric isomerism.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010204
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  • 12
    Electronic Resource
    Electronic Resource
    The metabolism of trimipramine in the rat (1990)
    Chichester : Wiley-Blackwell
    Biological Mass Spectrometry 19 (1990), S. 793-806 
    Details
    ISSN: 1052-9306
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Studies on the metabolism of the tricyclic antidepressant trimipramine, 5-(3-dimethylamino-2-methylpropyl)-10, 11-dihydro-5H-dibenz[b, f] azepine, in the rat are described. Many metabolites of trimipramine (TMP) were isolated from rat urine after enzymatic hydrolysis and their structures were identified by a gas chromatographic/mass spectrometric method, before and after appropriate chemical derivatization. Besides unchanged TMP, 20 metabolites were characterized (underivatized, and after acetylation), of which 12 had undergone alicyclic (C10 or C11) oxidation. This is a hitherto unreported metabolic pathway for TMP in the rat.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/bms.1200191303
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  • 13
    Electronic Resource
    Electronic Resource
    A re-examination of the synthesis and some properties of the in vitro metabolite, N-hydroxyphenmetrazineAbbreviation: CPBA = m-chloroperbenzoic acid. (1975)
    Chichester : Wiley-Blackwell
    Biological Mass Spectrometry 2 (1975), S. 137-141 
    Details
    ISSN: 1052-9306
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reported synthesis of N-hydroxyphenmetrazine from phenmetrazine by the action of m-chloroperbenzoic acid could not be repeated. When the synthetic procedure was modified N-hydroxyphenmetrazine was obtained in low yield. The product had different properties from those claimed previously, but was identical to metabolically produced N-hydroxyphenmetrazine. It was characterized by means of thin-layer chromatography, combined gas chromatography and mass spectrometry, preparation of a t-butyldimethylsilyl derivative and oxidation to a mixture of nitrones. Mass spectrometry was also used to characterize these derivatives.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/bms.1200020307
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  • 14
    Electronic Resource
    Electronic Resource
    Mass spectra of 2H-1,4-benzoxazine and-benzothiazine hydroxamic acids (1970)
    Chichester : Wiley-Blackwell
    Biological Mass Spectrometry 3 (1970), S. 105-118 
    Details
    ISSN: 0030-493X
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The mass spectra of various benzoxazine and benzothiazine hydroxamic acids and related lactams have been recorded and interpreted. Proposed fragmentations have been substantiated by means of deuterium-labeling and accurate mass measurements. Abundant molecular ions were observed in all spectra. The benzoxazine hydroxamic acids fragmented initially by expelling an oxygen atom and a COOH radical from the molecular ion. The corresponding benzothiazine hydroxamic acids lost an oxygen atom and an OH radical, whereas their 1,1-dioxides decomposed by losing an oxygen atom and a ketene or substituted ketene molecule. The expulsion of CO, HCN, CS and SO2 molecules, as well as alkyl and NO radicals were common subsequent fragmentations.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/oms.1210030113
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  • 15
    Electronic Resource
    Electronic Resource
    The fragmentation of ortho-methoxyphenyl-2-propanone oximes and related compounds-further examples of an ortho-effect (1973)
    Chichester : Wiley-Blackwell
    Biological Mass Spectrometry 7 (1973), S. 985-988 
    Details
    ISSN: 0030-493X
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: An [M — 31]+ ion was a prominent fragment in the mass spectra of three ortho-methoxy-phenyl-2-propanone oximes and is shown to be due to the expulsion of a methoxyl radical from the molecular ion as a result of an ortho-effect. In contrast, an [M — 31]+ ion was absent from the spectra of a structurally related ketone and a hydroxylamine, and was not observed in the spectra of meta- and para-methoxyphenyl-2-propanone oximes.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/oms.1210070808
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  • 16
    Electronic Resource
    Electronic Resource
    The mass spectra of succinimides, hydantoins, oxazolidinediones and other medicinal anti-epileptic agents (1970)
    Chichester : Wiley-Blackwell
    Biological Mass Spectrometry 3 (1970), S. 735-745 
    Details
    ISSN: 0030-493X
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The mass spectra of the following common anti-epileptic agents; phensuximide, methsuximide, ethosuximide, ethotoin, mephenytoin, diphenylhydantoin, trimethadione, paramethadione, primidone and phenacemide, have been recorded and interpreted. In addition the mass spectra of succinimide, α-phenylsuccinimide and the N-deuterated derivative of ethotoin were studied. The investigated compounds fragment in an interesting manner and give rise to stable ions by which means they are readily identified. The most diagnostic fragmentation in the majority of the spectra was the expulsion of a (CO)2NR fragment from the molecular ion.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/oms.1210030605
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  • 17
    Electronic Resource
    Electronic Resource
    Mass spectra of selected beta-carbolines [β-9H-pyrido(3,4-b)indoles] (1970)
    Chichester : Wiley-Blackwell
    Biological Mass Spectrometry 3 (1970), S. 879-889 
    Details
    ISSN: 0030-493X
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The mass spectra of fifteen β-carbolines have been interpreted and proposed fragmentations have been substantiated by means of deuterium-labeling and accurate mass determinations. Most decompositions were predictable. An interesting fragmentation was observed in the spectra of 1-alkyl-1,2,3,4-tetrahydro-β-carbolines, which rearrange to expel an alkylamino (RNH) radical from the molecular ion.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/oms.1210030706
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  • 18
    Electronic Resource
    Electronic Resource
    Identification of the aromatic hydroxylamine group by mass spectrometry (1970)
    Chichester : Wiley-Blackwell
    Biological Mass Spectrometry 3 (1970), S. 63-65 
    Details
    ISSN: 0030-493X
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The mass spectra of aromatic hydroxylamines are diagnostic; [M], [M - 2], [M - 16] and, in most instances, [M - 17] ions are observed.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/oms.1210030108
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  • 19
    Electronic Resource
    Electronic Resource
    Mass spectra of some quinoline hydroxamic acids and related compounds (1969)
    Chichester : Wiley-Blackwell
    Biological Mass Spectrometry 2 (1969), S. 681-695 
    Details
    ISSN: 0030-493X
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The mass spectra of some 3- and 4-substituted quinoline hydroxamic acids and related compounds have been interpreted, and proposed fragmentations substantiated by means of deuterium-labeling and accurate mass determinations. All compounds examined gave abundant molecular ions; most showed strong [M — 16]+ ions and weak [M — 17]+ ions. The expulsion of CO and HCN molecules and H and HCO radicals were common subsequent decompositions. The spectrum of 4-hydroxy-2-methylquinazoline-3-oxide (VII) was unique and showed that nitric oxide was expelled from the molecular ion.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/oms.1210020703
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  • 20
    Electronic Resource
    Electronic Resource
    Identification of a nitrone as an in vitro metabolite of N-methylamphetamineAbbreviation: NMA = N-methylamphetamine. (1978)
    Chichester : Wiley-Blackwell
    Biological Mass Spectrometry 5 (1978), S. 418-422 
    Details
    ISSN: 0306-042X
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The relatively labile nitrone, α-methyl-(N-methylene)benzeneethanamine N-oxide was isolated from incubates of (±)-N-methylamphetamine with fortified liver homogenates from rats and rabbit. Identification of the nitrone was confirmed directly by gas chromatography and gas chromatography mass spectrometry and, after its conversion to isoxazolidine adducts by the action of methyl and ethyl acrylate. An authentic sample of the nitrone was synthesized unequivocally from N-hydroxyamphetamine and formaldehyde. The isomeric nitrone, N-(α-methylbenzeneethylidene)methylamine N-oxide, was also synthesized and its gas chromatographic and gas chromatographic mass spectrometric characteristics determined to confirm that the metabolically formed nitrone was not N-(α-methylbenzeneethylidene)methylamine N-oxide. Two previously unreported metabolites of (±)-N-methylamphetamine, N-hydroxyamphetamine and 1-hydroxy-1-phenyl-2-propanone, were isolated from rat in vitro experiments; the latter metabolite was not produced in vitro by rabbit liver homogenates.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/bms.1200050609
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